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Reaction of diazoacetone, methyl diazoacetate, and dimethyl diazomalonate with 2-ethoxycarbonyl and 2-cyanofurans in the presence of rhodium acetate

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The reaction of 2-ethoxycarbonylfuran with diazoacetone and methyl diazoacetate in the presence of rhodium acetate at 20°C gives bicyclic adducts of the corresponding carbenes at a furan ring double bond in 18–22% yield with the complete absence of products of opening of the furan ring (acyclic oxodienes). In analogous reactions, 2-cyanofuran gives derivatives of 5-(2-furyl)oxazoles in yields up to 55%, which are the products of the 1,3-dipolar cyclo-addition of the carbenes at the cyano group in addition to the bicyclic adducts in 12–17% yields.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    L. E. Saltykova, A. E. Vasil'vitskii, V. M. Shostakovskii & O. M. Nefedov

Authors
  1. L. E. Saltykova
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  2. A. E. Vasil'vitskii
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  3. V. M. Shostakovskii
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  4. O. M. Nefedov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2833–2836, December, 1988.

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Saltykova, L.E., Vasil'vitskii, A.E., Shostakovskii, V.M. et al. Reaction of diazoacetone, methyl diazoacetate, and dimethyl diazomalonate with 2-ethoxycarbonyl and 2-cyanofurans in the presence of rhodium acetate. Russ Chem Bull 37, 2557–2560 (1988). https://doi.org/10.1007/BF00952639

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  • DOI: https://doi.org/10.1007/BF00952639

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